Electrogenerated base (EG base) induced hydroxymethylation of the side chain of nitroalkylbenzenes with paraformaldehyde

Sigeru Torii, Yasuo Murakami, Hideo Tanaka, Koichi Okamoto

Research output: Contribution to journalArticle

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Abstract

Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n-DMF-Et4NOTs-(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.

Original languageEnglish
Pages (from-to)3143-3147
Number of pages5
JournalJournal of Organic Chemistry
Volume51
Issue number16
Publication statusPublished - 1986

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Electrolysis
Formaldehyde
Electrolytes
Derivatives
Electrodes
Catalysts
paraform

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Electrogenerated base (EG base) induced hydroxymethylation of the side chain of nitroalkylbenzenes with paraformaldehyde. / Torii, Sigeru; Murakami, Yasuo; Tanaka, Hideo; Okamoto, Koichi.

In: Journal of Organic Chemistry, Vol. 51, No. 16, 1986, p. 3143-3147.

Research output: Contribution to journalArticle

Torii, Sigeru ; Murakami, Yasuo ; Tanaka, Hideo ; Okamoto, Koichi. / Electrogenerated base (EG base) induced hydroxymethylation of the side chain of nitroalkylbenzenes with paraformaldehyde. In: Journal of Organic Chemistry. 1986 ; Vol. 51, No. 16. pp. 3143-3147.
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